HCID 66728607, compound → HCID 21873802, compound

HRID 518639Notes

Reaction equation

HRID 518639 reaction equation
C([NH:8][CH:9]1[CH2:14][CH2:13][C:12]([OH:18])([C:15]([OH:17])=[O:16])[CH2:11][CH2:10]1)C1C=CC=CC=1>[Pd].CCO>[NH2:8][CH:9]1[CH2:14][CH2:13][C:12]([OH:18])([C:15]([OH:17])=[O:16])[CH2:11][CH2:10]1

Participants

4

Reactant 1

HCID 66728607HCID 66728607, compound

Product 1

HCID 21873802HCID 21873802, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

4-(Benzylamino)-1-hydroxycyclohexanecarboxylic acid (0.44 g, 1.765 mmol) and 10% palladium on carbon (0.282 g, 0.265 mmol) were charged into a round bottom flask under nitrogen atmosphere. To this was added EtOH (8.82 mL), and the mixture was stirred under an atmosphere of hydrogen at RT for 72 hours. The mixture was diluted with EtOH (10 mL) and filtered through Celite® brand filter aid, rinsing with DCM (10 mL), EtOH (10 mL), and MeOH (10 mL). The filtrate was concentrated under reduced pressure to afford 4-amino-1-hydroxycyclohexanecarboxylic acid as a yellow solid (0.28 g, 100% yield). MS m/z=160.2 [M+H]. Calc'd for C7H13NO3: 159.1.

Workup

  1. filtrationfiltered through Celite® brand
  2. filtrationfilter aid
  3. washrinsing with DCM (10 mL), EtOH (10 mL), and MeOH (10 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ff6e334f11e94c03acda85d473877249
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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